The Contest Winner
by ShipsInTheKnight
Summary: When famous singer Regina Mills offers an opportunity for one of her fans to join her on tour, Emma's best friend Ruby jumps at the chance, whereas Emma couldn't care less about it. When it turns out they've won the contest, Ruby and Emma are flown out to meet Regina. After getting the chance to meet her in person, Emma begins to wonder if maybe they're not so different after all.
1. Chapter 1

"I mean, who does she think she is? Some kind of queen?" complained Emma, referencing toward the small television set in her one-bedroom apartment.

After swallowing another handful of popcorn, Emma's best friend Ruby replied, "I know you don't like her, Ems, but you gotta admit she's super hot." Emma growled in response as she continued watching the brunette's performance come to an end.

 _"Another round of applause for the lovely and talented Regina Mills, everybody!" the host announced. The crowd went wild as the woman bowed and then made her way off stage._

"Thank God!" exclaimed Emma over dramatically, causing the other girl present to roll her eyes. "What? Now we get to watch more of the show!"

It had become a tradition for the two girls to spend every Saturday night together eating popcorn as the latest episode of Saturday Night Live aired. Regina Mills had been the guest performer scheduled for the night.

"Ooh! She just posted a tweet!" Ruby squealed as she tapped to view favorite music artist's newest post.

"Let me guess, another one about her precious tour?" Emma took a large swig from her bottle of root beer.

Having expected an eye roll or rebuke, Emma's attention was drawn when no response came. "What does it say?"

Unable to find her voice, Ruby turned her phone screen toward Emma, who began to read, _"As a thank you to all my fans, I've decided to invite one of you to join me for part of my tour! Look out for more information soon!"_

Glancing back toward her friend, Emma watched as the girl's face broke out into large, toothy smile. "Come on, Rubes. You don't _really_ believe that, do you? They'd never let someone like her invite a complete stranger on her tour."

"Even if it's not possible, I'm still going to try," Ruby replied with a hopeful expression. "Who knows? Maybe I'll win a free t-shirt or something."

As the show returned from a commercial break, the two girls' attentions were brought back to the glowing screen.

* * *

 **Granny's Diner - One Week Later**

"Emma! Emma!" yelled a frantic Ruby as she raced toward the blonde, who was sitting in a booth on the opposite side of the diner. After taking a seat across from her friend, Ruby glanced toward the kitchen where her granny was flashing her a disapproving look.

"Whoa, what's going on, Rubes?" Emma had been startled by the other girl's sudden appearance, having fully expected to eat her lunch of grilled cheese in peace.

"She's posting the winner tonight!"

Ruby's reply only confused the blonde further. "What are you talking about?"

"Do I have to spell it out for you? Regina Mills is posting the winner of her fan contest _tonight!"_ Ruby squealed, causing Emma to wince at the high-pitched noise. "Just think, in a few hours I could get recognized by the queen herself!"

"Okay, this is getting out of hand, Ruby. You do know she's just a person like everyone else, right?" Emma's voice took on its usual annoyed tone for whenever the star was mentioned.

"But she's not, Em! You don't understand. She's my–"

"Ruby!" the elderly woman from the kitchen called out. "Get over here! It's time for your shift."

Frowning, Ruby stood from her seat and made her way toward the kitchen door. Before entering, the girl paused on a whim and turned back toward the blonde, saying, "Just you wait and see. I _will_ meet Regina Mills."

After she had disappeared into the kitchen, Emma couldn't hide the snort of disbelief that escaped her at her friend's naïve comment. Emma knew better than anyone that the chances of meeting one's favorite celebrity was slim to none.

* * *

 **Emma's Apartment - Later That Day**

"Haven't you ever heard the phrase 'a watched pot never boils'?" Emma teased.

Ripping her gaze from the clock on her phone, Ruby playfully narrowed her eyes at her friend. Before she could open her mouth to retort, a loud ding erupted from her cell phone–signaling a twitter update from her favorite celeb.

The brunette snatched her phone from the table and rushed to view the tweet, her fingers shaking with anticipation. Emma eyed her friend warily and she dreaded having to watch the scene unfold, knowing that it was not going to play out in girl's favor.

 _"I'm pleased to announce that the winner of my randomized fan giveaway is,"_ Ruby read quickly to herself, anxious to get to the big reveal. When her eyes were met with the first letter of the name, her heart dropped to her stomach.

She knew it was all over.

Her expression fell and she felt as if the wind had been knocked out of her. Having expected this reaction, Emma was quick to comfort her friend.

"Aw, it's okay, Rubes. We can't win them all," Emma attempted to soothe as a single tear trailed down her friend's cheek.

"I-I know," Ruby sobbed out. "It's just–"

"She's your favorite. I get it." After a pause, Emma asked, "Who _did_ win?" She had no clue why she was so curious. "Maybe we can stalk and make fun of them if it helps?" Emma rushed to explain. The blonde's comment managed to get the other girl to smile, even if it was only for a second.

Glancing back down at her phone, Ruby wiped a tear drop that had covered the winner's name and then announced weakly, "Some bitch named Emma Swan."

There was a brief pause as the name and meaning behind it registered with the two women, and then–

"OH MY GOD, EMMA! YOU WON!"


	2. Chapter 2

"H-how is this even possible?" Emma was just as shocked by the news as Ruby.

After having been lost deep in thought, the brunette gasped in realization. "Do you remember that night we went to the Rabbit Hole?"

"You mean when we got so drunk we were surprised we made it back in one piece?"

The waitress nodded. "You may not remember much, but in my drunken state I remember talking you into entering the contest," Ruby revealed.

"You did _what?!"_ Emma shouted.

"I thought it'd be funny? I don't know! I was drunk!"

"And now I've won the chance to go on tour with Regina Mills," Emma finished. After a pause, she added, "What if I don't want to go?"

"You have to! You can't just refuse!" Ruby was stunned by the blonde's lack of enthusiasm towards winning. Even if Emma _did_ dislike the celebrity as much as she claimed, wouldn't it give her at least bragging rights? Ruby began to wonder if Emma truly had something against the star.

The brunette shook the thought from her head and then continued to speak. "Besides, I happen to know the perfect person you could bring along as your plus one; someone who's been dying for a chance to meet Regina Mills," Ruby grinned knowingly.

Emma knew she couldn't argue back, not when she knew how much this adventure would mean to the young waitress. And Ruby's has always been such an amazing friend to her.

So, Emma agreed to go on the trip with Ruby.

* * *

 **New York Airport – One Month Later**

Emma watched as the lanky brunette made her way toward her while struggling to balance all her luggage.

"Shit, Ruby. Got enough bags?"

The other girl placed her items on the ground and then let out a sigh of relief. "I have to look my best if I'm going to meet _the queen,"_ she grinned.

Ever since the announcement of the trip, Ruby's been referring to the star as 'the queen' just to mess with the blonde.

Emma rolled her eyes in response to the title and then the overhead speaker announced that their plane was now boarding. "Yeah, yeah. Now let's go before you miss your 'chance of a lifetime'."

* * *

Their flight from New York to California was unlike any either of the girls had ever experienced. Regina Mills's assistant had arranged for them to have first class tickets, which allowed them the best seats on board, along with an unlimited movie selection.

Knowing the flight would take around six hours, Emma and Ruby had pre-planned their activities. Emma began the flight by taking a two-hour nap, since her sleep was cut short due to the early flight, and then she planned on watching action and comedies until they landed.

As for Ruby, she planned on staying awake then entire time, not wanting to miss out on a minute of it. She enjoyed the free refreshments and watched as many cheesy, romantic comedies as she could before they arrived in Los Angelos. Needless to say, both women were extremely happy when they un-boarded the plane.

After receiving their baggage, they met their chauffeur for their journey. He was a kind, elderly man who insisted they refer to him by his first name–Henry.

Henry assisted with loading their luggage into the trunk of his luxurious black sedan and then gave the two girls a short tour of the city. Ruby and Emma rolled down their windows and basked in the moment, both having never visited California before. Henry couldn't help but let out a few chuckles at the girls' reactions.

After the tour, Henry pulled the car up in front of a large iron gate and both Emma and Ruby were intimidated by the sight. After announcing their presence, the gate opened before them and both of the girls' jaws hit the inside flooring of the sedan.

The car proceeded forward and the two looked on in awe at the large mansion they had arrived at. They felt the vehicle slow to a stop and their doors were immediately opened by two nicely-dressed gentlemen. After sharing a look, they exited the vehicle and Henry reminded them that their bags were to be taken care of for them.

Having awaited their arrival, an attractive man with dark brown hair descended the main stairs, leading up to the mansion's entrance, and introduced himself.

"Hello, ladies. My name is Graham. I believe you know me to be Regina's assistant and we've spoken on the phone." Emma nodded in confirmation. Both of them were still trying to convince themselves that this was all really happening.

Smiling to the two women, the man continued, "If you could follow me this way. Miss Mills has been expecting you."

Once again the pair shared a look and then followed him as he led them into the mansion. When they had fully entered the building, Ruby and Emma's eyes lit up at the glorious black and white décor of the home. Emma couldn't help but to compare it to her own place back in New York, which only reminded her further of how temporary this all was.

Graham allowed them to scan the interior for a moment, knowing how striking it could be for those who had never visited before, and then he guided them toward the back patio where he knew his boss to be located.

When the trio had passed through the elegant double doors leading to the outside, Emma's gaze was immediately caught by the celebrity herself rising from the waters of her pool, her body drenched and clad in only a white bikini. Emma couldn't help but gawk at the woman's beauty.

Meeting her new visitors' gazes, seemingly unconcerned by her lack of clothing, Regina Mills greeted the two with a wide smile. "You must be Emma Swan. It's a pleasure to meet you," she extended her hand toward the brunette, who unconsciously responded in kind before kicking herself out of her stupor.

"Actually, she's Emma Swan. I'm Ruby, her friend." Ruby blushed furiously at the mistake, thankful that the celebrity had already turned her attention to the woman beside her before she could further embarrass herself in front of her idol.

Emma gulped before offering the woman a small wave. "Hi."

Taking in the sight of the woman now standing before her, Regina smiled appreciatively. "You've made good timing, Miss Swan. You two are just in time for lunch."

Turning toward her assistant, she directed the man, "Graham, please take these two to their rooms while I get changed." The assistant acknowledged her order as she strutted past them, wrapping a towel around her midsection as she made her way back inside the mansion.

Directing his attention back to the two girls, he inquired with a knowing look, "Who wants to see their rooms?"


	3. Chapter 3

After receiving a brief tour from Graham and locating their rooms, Emma and Ruby's stomachs began begging for attention.

"Don't worry. You'll love the menu Regina has prepared for today," the assistant commented as the trio descended the main stairs of the mansion. "Belle, her personal chef, is by far one of the best I've ever encountered." Craning his neck toward the lighter-haired of the two women, he added, "And Regina _always_ has the best."

Taking in all the fanciful décor for the second time, Ruby snorted, "That's for sure."

Following Graham's lead, they made their way to the main dining hall and were met inside by the sight of Regina, who was sitting gracefully at the head of the long oval-shaped table.

No longer clad in her bathing suit, the celeb wore an elegant white jumpsuit with golden accessories, and her previously wet hair was slicked back by a thin layer of product.

"Ah, there you are," greeted the woman, her painted red lips spreading out into a grin. "Please, take a seat wherever you choose. This is, after all, your new home for the next few days before we leave for tour."

Ruby and Emma hesitantly took a seat on either side of the celebrity, now feeling far more intimidated being in singer's presence–due to the woman's change of attire.

A long, drawn out lull in conversation followed the two sitting down, which visibly seemed to displease Regina.

Deciding to bring the silence to an end, the singer cleared her throat and gave her assistant the signal to have their meal be presented.

Seconds later, platters full of freshly prepared fruits, pastas, and vegetables began covering every inch of the table. Both Emma and Ruby's senses were overwhelmed by the vast array of colors, smells, and sounds of the food being placed before them. They were in–what Emma would call–food heaven. Minus the bear claws and grilled cheese, of course.

As Ruby immediately began digging in, Emma remained still, her eyes still engulfing all that was before her. Her mind flashed to old, forgotten memories of growing up in foster homes with not enough food on the table and she immediately felt guilty.

"Something wrong, dear?" Regina questioned with a quirk of a brow.

After bringing herself back to reality, Emma shook her head. "No. Everything's fine. This is just…a lot to take in."

Her answer seemed to be enough for Regina, who then nodded in understanding and began gathering her own plateful of fruits and homemade pasta.

Exhaling, Emma picked up one of the wooden serving spoons and plopped a small helping of pasta primavera onto her plate, followed by a few orange slices. Even though her feeling of guilt failed to subside, Emma didn't want another one to come on by appearing to be a rude guest.

After the meal was over, Regina announced that she had an extremely busy schedule planned for the rest of the day, which translated to Emma and Ruby as them needing to find their own way of entertaining themselves before her return.

Having never experienced walking along the sandy beaches of California, Ruby and Emma decided amongst themselves to do that first. Thankfully, Regina allowed Henry to remain with them, providing them with a means of transportation.

* * *

When they had arrived at the Santa Monica pier, the two girls stripped down until they were clad in only their suits and then rushed into the water–the waves crashing against their bare skin.

After an hour of running along the beach, building a sorry excuse for a sand castle, and swimming in the water, Emma and Ruby were exhausted. They collapsed onto a large colorful blanket they had borrowed from Regina, and smiled up at the sunlight pouring down on them.

Turning to her best friend, Ruby asked casually, "So what was with you during lunch?"

"What do you mean?"

Propping herself up on her elbows, Ruby explained, "You seemed quieter than usual. I know Regina Mills isn't exactly your favorite person, but I thought you'd at least say _something._ "

After a pause, Ruby chuckled to herself. "I was half convinced you were waiting until the end to go off on some long, feminist rant about the messages behind her songs."

Emma responded with a noncommittal shrug and said, "I guess I just wasn't feeling it."

"No, something's bothering you." Ruby narrowed her eyes at the blonde. "I can always tell with you. You're not that good of a liar."

"Fine. I was a bit upset by the amount of food that was there," Emma admitted. Catching Ruby's confused expression, she added, "You know, because of how I grew up?"

It took a second, but once it registered Ruby's eyes grew wide in realization. "Oh god, Ems. I'm sorry."

Seeing the honestly in her friend's expression, Emma waved the girl off. "It shouldn't even upset me anymore. I thought I'd be over things like that by now, but–"

"No, Em. You're allowed feel the way you do. That extra food could go to charity, but instead it's thrown in the trash. Maybe _that's_ something you can talk to her about?" Ruby tried.

Emma couldn't help the smile tugging at the corner of her mouth at her friend's comment.

After beginning to feel the heat's effect on their skin, Emma and Ruby decided to call it a day and return to the mansion.

* * *

When they arrived back, Emma noticed Regina's car had returned to its previous spot in the driveway.

The two thanked Henry again for the ride and allowed one of Regina's security men to open the entrance door for them to go inside. Immediately, Ruby excused herself to take a shower–wanting to wash out the seawater as quick as possible–resulting in Emma being left alone in the main foyer.

Before, Emma hadn't had the opportunity to take in the finer details of the home. Glancing around, her sight was drawn to a framed photo, which appeared out of place for the seemingly impersonal décor.

Taking the object into her hands, Emma took in the sight of a child-like version of Regina Mills, who was standing upon a platform with a microphone and a bright-pink boa wrapped around her neck.

"That's me backstage during one of my mother's performances," rang a voice from behind her, causing Emma to almost drop the glass frame out of shock. The near accident was lost on Regina, whose mind was caught back in a distant memory.

Chuckling to herself, Regina explained, "I used to lip-sink to my mother's songs as they were performed. The laughter and smiles I received doing that was one of the things that made me want to follow in her footsteps."

Tearing her gaze from the photo, Emma's eyes met the singer's and she saw nothing but pure honestly reflecting back at her. Feeling the need to say something– _anything_ –Emma began, "That's..." but she was unable to find her words.

Breaking the eye-contact, Regina glanced away from the blonde and wiped a tear from her eye. "I should probably get back to my studio."

"Right. Of course," Emma responded, restoring the photograph to its proper location. Pointing awkwardly toward the staircase, she added, "Ruby's waiting for me, so…"

Their eyes met once again and both women felt frozen on their feet, unable to move. After a beat, Regina shook herself from her stupor, strutting off toward the direction of her studio, and Emma made her way up the stairs. On her way back toward the guest room, she couldn't help but wonder what the _Hell_ just happened between them.


	4. Chapter 4

Closing the door to her studio behind her, Regina let out a breath she wasn't aware she was holding in.

She had never been so willing to open herself up to anyone before, especially someone she's known for less than a day. But for some reason, Regina felt drawn to the blonde woman.

The singer made her way to her grand piano and began playing a melody, in attempts to clear her head, but it only made her reflect more on her day.

All during their lunch, Emma had seemed distracted as her friend went on asking the star any question that popped into her mind. Though Regina knew not everyone who enjoyed her music was a super fan, such as Ruby, she had thought the blonde would be more enthusiastic about winning the chance to meet her.

Although Regina would never admit it aloud, she had done her research on her contest winner before she arranged her visit. In her mind, she wrote it off to pure curiosity and not wanting to invite a serial killer into her home, despite her employees already having done a background check on the woman.

As she searched through any social media page she could find belonging to the blonde, Regina found herself laughing at the ridiculous things the woman would post. The genuine bout of laughter that erupted from the singer, due to finding a video of Emma and Ruby performing drunk karaoke, made Regina realize that she hadn't laughed so hard in a long time.

To her, the blonde seemed genuine in a world full of people just trying to impress, and the fact intrigued Regina.

* * *

The next day Emma and Ruby woke up to their phone alarms, which they had set so they wouldn't miss breakfast. After getting ready for the day, each dressing casually in shorts and a tank top, they made their way downstairs to eat.

Yawning, despite it already nearing eleven o'clock, Emma took her seat at the table–the same one from the previous day. And Ruby did the same.

"Glad to see you're both alive and well," smirked the star as she entered the room. Regina was wearing a salmon-colored skirt, a black halter top, and a pair of matching black heels.

"Didn't peg you as a morning person, Mills," joked Ruby, feeling much more comfortable around the star.

"Oh, I'm not," the singer was quick to correct. She took her seat at the head of the table. "Unfortunately, being famous means the latest you can sleep in is nine o'clock. I had a meeting with my personal trainer this morning, followed by a date with some magazine editor."

"A date?" Emma's blurted out before her mind could stop her.

Smirking once again, Regina nodded. "Yes, dear. Though, it was more of a business arrangement. They want me to be the new face of Vogue," the woman waved off.

"Vogue?" Ruby gasped. Emma wondered if her friend would pass out from lack of oxygen.

Regina smiled at the girl's reaction and watched as her staff laid down their meals. After nodding to them that the food was satisfactory, Regina took a bite of her personal tomato and basil omelet.

Following her lead, Ruby and Emma did the same with their food, having ordered what they wanted the previous day. While Ruby opted to eat whatever Regina was having, Emma decided to play it safe and order plain buttermilk pancakes for herself, loaded with extra butter.

"So, what are your plans for the rest of the day?" Ruby asked the other brunette between bites.

Wiping the corners of her mouth with a napkin, Regina replied, "I've made sure my schedule was clear, so we all could get to know each other." After casting a quick glance in the blonde's direction, Regina added, "I was thinking we could relax by the pool. It's really up to you two to decide."

Ruby grinned from ear to ear at the thought of being in charge of Regina Mills' day, even if it was just for a few hours. Turning her attention to the blonde across from her she said, "What are you thinking, Ems?"

At the nickname, Emma glanced up from cutting herself another bite, and then tilted her head in thought. "I guess I'd be fun to go swimming at a millionaire's house."

While Ruby's smile grew at the response, Regina's faded into a frown. For some reason, she felt the need to please the blonde.

* * *

After they had finished their meals, all three women returned to their respective rooms to change into their swim attire–having decided on relaxing by the pool for the day's activity.

Ruby did a double take as she walked by her friend's room and saw Emma glaring at her own reflection in the mirror. It wasn't like her friend to be so self conscious about her appearance. In fact, she usually bragged about it and would flash anyone her toned stomach if they ever questioned her eating habits.

"You okay, Ems?" The blonde jumped at her friend's words, having not expected her presence.

Emma wanted to lie to her friend again and tell her everything was fine, but she knew Ruby would see right through it. Turning toward her friend, Emma confessed, "I'm nervous, okay?" Then she ran her fingers through her long, blonde locks.

Ruby made her way toward the shorter woman and wrapped her in her arms. "Aw, Em. It's okay. You look great," she attempted to soothe.

"It's not about how I look. It's…Regina." Emma mumbled under her breath, her words almost going unheard by the brunette.

Ruby furrowed her brows for a moment before realization dawned on her. "You like her." Her tone was void of judgment, as if she were plainly stating a fact.

Emma shook her head at first but then nodded in resignation.

"That actually explains a lot," Ruby thought out loud, resulting in a slight push of her shoulder. She chuckled at the action. "Don't worry, Swan. Your secret is safe with me." The brunette winked at her friend before exiting the room, giggling to herself.

Emma let out a little noise of amusement, as well, at the absurdity of it all. How can a little celebrity crush make her feel so nervous inside? She attempted to push her feelings aside and followed her friend toward the back porch, where she knew the pool to be located.

Hopefully, whatever she felt toward the woman would soon fade.


End file.
